Hydrochloric Acid → HCID 13288304, compound

HRID 1078343Notes

Reaction equation

HRID 1078343 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH2:19][CH2:20]Cl)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18].Cl>C(N(CC)CC)C>[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH2:19][CH2:20][N:5]2[CH2:6][CH2:7][CH2:8][CH:3]([CH2:2][OH:1])[CH2:4]2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 107308Piperidin-3-ylmethanolHCID 30153594-(2-Chloroethyl)-1,2-dimethoxybenzene2×

Product 1

HCID 13288304HCID 13288304, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 5.75 g of 3-(hydroxymethyl)piperidine, 13.8 ml of triethylamine and 10 g of 2-(3,4-dimethoxyphenyl)-ethyl chloride was heated under reflux for 4 hours. After the reaction mixture had cooled, it was acidified with about 30 ml of aqueous 2N hydrochloric acid solution, and unreacted 2-(3,4-dimethoxyphenyl)-ethyl chloride was separated by extraction with tert-butyl methyl ether. The aqueous phase was then rendered alkaline by addition of sodium hydroxide solution and was extracted with dichloromethane. The organic phase was separated, dried and concentrated. 5.3 g of N-[2-(3,4-dimethoxyphenyl)-ethyl]-3-(hydroxymethyl)-piperidine were obtained.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter the reaction mixture had cooled
  4. customwas separated by extraction with tert-butyl methyl ether
  5. additionby addition of sodium hydroxide solution
  6. extractionwas extracted with dichloromethane
  7. customThe organic phase was separated
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-22f68e580c6f4dcea6f51842199232dd
Source dataset
uspto-grants-1996_08
Patent number
US05547967

Reaction notes

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